Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

5. Chirality

R and S Configuration

Organic Chemistry

5. Chirality

R and S Configuration

Previous problemNext problem

3:57 minutes

Problem 10a

Textbook Question

Given the following IUPAC names, draw the corresponding structures.
(a) (R)-3-isopropyl-6-methylnon-1-ene

Verified step by step guidance

Step 1: Start by identifying the parent chain. The name 'non-1-ene' indicates a nine-carbon chain with a double bond starting at the first carbon. Draw a straight chain of nine carbons and place a double bond between C1 and C2.

Step 2: Add substituents to the parent chain. The name '3-isopropyl' indicates an isopropyl group attached to the third carbon of the chain. Draw a branch consisting of two methyl groups attached to the third carbon.

Step 3: Add the second substituent. The name '6-methyl' indicates a single methyl group attached to the sixth carbon of the chain. Draw a methyl group branching off from C6.

Step 4: Assign the stereochemistry. The '(R)' configuration specifies the absolute configuration at the chiral center. Identify the chiral center (C3, where the isopropyl group is attached) and arrange the substituents such that the priority rules (Cahn-Ingold-Prelog) are followed to achieve the (R)-configuration.

Step 5: Verify the structure. Ensure the double bond is correctly placed, the substituents are accurately positioned, and the stereochemistry matches the (R)-configuration. Confirm that the structure corresponds to the given IUPAC name.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming organic chemical compounds. It provides a set of rules to derive the name from the structure, ensuring that each compound has a unique and descriptive name. Understanding the components of the name, such as the longest carbon chain, substituents, and stereochemistry, is essential for accurately drawing the corresponding structure.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the given name, '(R)' indicates the specific three-dimensional configuration of the chiral center, which is crucial for determining the correct structure. Recognizing stereochemical descriptors is vital for accurately representing the compound's geometry.

Alkenes and Unsaturation

Alkenes are hydrocarbons that contain at least one carbon-carbon double bond, which introduces unsaturation into the molecule. The term 'non-1-ene' in the name indicates that the double bond is located at the first carbon of a nine-carbon chain. Understanding the properties and reactivity of alkenes is important for drawing their structures and predicting their behavior in chemical reactions.

Watch next

Master Why stereoisomers need their own naming system. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

In Problem 5-3, you drew the enantiomers for a number of chiral compounds. Now go back and designate each asymmetric carbon atom as either (R) or (S).

(c)

(d) 1-bromo-2-methylbutane

Textbook Question

In Problem 5-3, you drew the enantiomers for a number of chiral compounds. Now go back and designate each asymmetric carbon atom as either (R) or (S).

(a)

(b)

Textbook Question

3,4-Dimethylpent-1-ene has the formula CH₂=CH—CH(CH₃)—CH(CH₃)₂. When pure (R)-3,4-dimethylpent-1-ene is treated with hydrogen over a platinum catalyst, the product is (S)-2,3-dimethylpentane.

c. The reactant is named (R), but the product is named (S). Does this name change imply a change in the spatial arrangement of the groups around the chiral center? So why does the name switch from (R) to (S)?

Textbook Question

Naproxen is a commercially available anti-inflammatory sold under the name Aleve.

(a) Assign the absolute configuration as R or S.

Textbook Question

Using IUPAC rules, name the following molecules.

(d)

Textbook Question

Given the name, draw the structure of the following compounds.

Textbook Question

Write structural formulas for the following compounds (includes both old- and new-style names).(j) vinylacetylene(k) (S)-3-methyl-1-penten-4-yne

Textbook Question

Write structural formulas for the following compounds (includes both old- and new-style names).